The processing of carbohydrates is crucially important in diseases such as diabetes, viral infections, and cancer. A key step in the processing of carbohydrates is the breakdown of bonds between the sugars. This breakdown is catalyzed by enzymes which can be inhibited by natural and synthetic compounds. Iminosugars, because they share structural features with sugars, are a promising class of compounds that inhibit these enzymes. The goal of this research was to synthesize two stereoisomers of tetrahydroxylated pyrrolizidines, a type of iminosugar. A six-step synthesis of intermediate 7 had previously been developed. This synthesis was repeated, and a ring closing metathesis, syn dihydroxylation, and acetylation steps yielded the desired intermediates 10 and 11. These two isomers were not successfully separated, but they may be able to be separated in future steps.

Steps toward the synthesis of tetrahydroxylated pyrrolizidines from L-glucose

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.